Pyrimidines

137281-39-1 , The common heterocyclic compound, 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, molecular formula is C15H14N4O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoic acid (38.4 mg, 0.129 mmol) in 5 mL of DMF was added N-methylmorpholine (40.4 mg, 0.399 mmol), followed by the addition of 2-chloro-4,6-dimethoxy-1,3,5-triazine (22.64 mg, 0.129 mmol). The resulting mixture was stirred for 1.5 hours at 25 !C, at which time HPLC showed that the reaction was complete. L-glutamic acid gamma-benzyl ester (30.6 mg, 0.129 mmol) was added, and stirring was continued at 25 !C until complete conversion of precursor was determined by HPLC (around two hours). To the reaction mixture was added 10 mL of methylene chloride and 10 ml of deionized water, and the mixture was stirred for 15 minutes. The layers were separated. The aqueous layer was extracted with DCM (10 ml*2). The organic phases were combined. The solution was concentrated on rotary-evaporator under reduced pressure. The resulting residue was subjected to flash chromatography on a Biotage system. Yield: 55 mg, 82%. 1HNMR in d6-DMSO, delta ppm: 10.61 (1H, s), 10.20 (1H, s), 8.72 (1H, d, J=10 Hz), 7.78 (2H, d, J=5 Hz), 7.35 (5H, m), 7.30 (2H, m), 6.30 (1H, s), 6.07 (2H, s), 5.14 (2H, s), 3.86 (1H, m), 2.97 (2H, t), 2.84 (2H, t), 2.20 (2H, s), 2.02 (1H, m), 1.95 (1H, m). ESI-MS: 518 [M+H]+.

The synthetic route of 137281-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF UTAH RESEARCH FOUNDATION; US2011/269713; (2011); A1;,
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611-08-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 611-08-5, name is 5-Nitrouracil, molecular formula is C4H3N3O4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: 2′,3′,5′-tri-O-Benzoyl-5-fluorouridine (3a)S1 (Table 2, entry 1). A mixture of5-fluorouracil (51.1 mg, 0.39 mmol), pyridine (0.6 mL), and hexamethyldisilazane(HMDS) (1.2 mL) was refluxed for ca. 40 min to give a clear solution of 2a. All thevolatiles were then removed under reduced pressure (ca. 1 mmHg) to give a clear syrup,which was dissolved in acetone (3.0 mL). To this were added1-O-acetyl-2,3,5-tri-O-benzoyl–D-ribofuranose (1) (151.8 mg, 0.30 mmol) and 7b (4.5mg, 0.015 mmol, 5 mol%) and the mixture was stirred under reflux for 6 h. After themixture was cooled to rt, it was diluted with EtOAc (2 mL), followed by the addition ofa saturated NaHCO3 aq (2 mL) at 0 C. After the mixture was stirred at 0 oC for 15min, EtOAc (30 mL) and a saturated NaHCO3 aq (20 mL) were added. The organicphase was separated and the aqueous phase was back-extracted with EtOAc (30 mL x 3).The combined organic layers were dried with Na2SO4 and evaporated to afford a crudematerial, which was purified by recrystallization from EtOAc (5 mL) and hexane (7mL) to afford 2′,3′,5′-tri-O-benzoyl-5-fluorouridine (3a) (152 mg, 88%) as a whitepowder.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 611-08-5, 5-Nitrouracil, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shirouzu, Hiroshi; Morita, Hiroki; Tsukamoto, Masaki; Tetrahedron; vol. 70; 22; (2014); p. 3635 – 3639;,
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696-45-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 696-45-7, name is 4-Amino-6-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

42.0 g of 4-amino-6-methoxypyrimidine (abbreviated as 4-MP, prepared according to Chinese patent CN 102516182) was added to 126 ml of pyridine at 0 to 5¡ãC, and 4-p-acetyl aminobenzenesulfonyl chloride (abbreviation SCL) 87.5 g. After the addition was complete, the reaction mixture was stirred at 20-30 ¡ã C until the 4-MP remained After completion of the reaction, 450 ml of ultrapure water was added and the supernatant was removed from the reaction mixture.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 696-45-7, 4-Amino-6-methoxypyrimidine.

Reference:
Patent; YWK CHEMICALS (TAICANG) CO., LTD; HAMADA, Shinichi; HAMADA, Tomoko; WANG, YINING; GUO, XIAOYE; CHANG, YONGKAI; CHEN, YAN; WEI, WENJUN; (6 pag.)CN105294576; (2016); A;,
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49845-33-2, A common compound: 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine,molecular formula is C4HCl2N3O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: The reaction of 2,4-dichloro-5-nitropyrimidine withisopropylamine produced intermediate 2-chloro-N-isopropyl-5-nitropyrimidin-4-amine. 4-Fluoronitrobenzene reacted with1-methylpiperazine in DMSO yielded the intermediate 1-methyl-4-(4-nitrophenyl)piperazine in the presence of K2CO3. The catalytichydrogenation of 1-methyl-4-(4-nitrophenyl)piperazine with palladiumon carbon (Pd/C, 5%) quantificationally provided thedesired 4-(4-methylpiperazin-1-yl) aniline. Refluxing of the 2-chloro-N-isopropyl-5-nitropyrimidin-4-amine with 4-(4-methylpiperazin-1-yl)aniline in n-butanol yielded N4-isopropyl-N2-(4-(4-methylpiperazin-1-yl)phenyl)-5-nitropyrimidine-2,4-diamine,which was reduced to intermediate A1 with a good yield by catalytichydrogenation using Pd/C as a catalyst. Intermediates A wereprepared as these steps and used for the next step without furtherpurification. These processes were carried out as reported.

With the rapid development of chemical substances, we look forward to future research findings about 49845-33-2.

Reference:
Article; Hei, Yuan-Yuan; Shen, Ying; Wang, Jin; Zhang, Hao; Zhao, Hong-Yi; Xin, Minhang; Cao, Yong-Xiao; Li, Yan; Zhang, San-Qi; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2173 – 2185;,
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130049-82-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, molecular formula is C11H15ClN2O2, molecular weight is 242.7, as common compound, the synthetic route is as follows.

Example 28.0L of methanol, 1.04 Kg (4.28 moles) of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-4H- pyrido[l,2-a]pyrimidin-4-one, 1.10 kg (10.89 moles) of triethyl amine and 1.0 kg (3.89 moles) of 6-fluoro-3(4-piperidinyl)-l,2-benzisoxazole hydrochloride were charged. The reaction mass was heated to reflux. The completion of reaction was monitored by HPLC. The reaction mass was cooled to 25-30C and further chilled to 0-5C, stirred for 30 min. and centrifuged. The cake obtained was washed with 0.5 L of chilled methanol. Weight of wet product containing paliperidone and inorganic salts was 1.0 kg, HPLC purity of paliperidone: 98.88%, keto- paliperidone impurity: 0.05%. The wet product obtained was further used for purification process.

Statistics shows that 130049-82-0 is playing an increasingly important role. we look forward to future research findings about 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; MEGAFINE PHARMA (P) LTD.; MATHAD, Vijayavitthal Thippannachar; SOLANKI, Pavankumar Vrajlal; SEKHAR, Babu Uppelli; PANDIT, Bhushan Sudhakar; WO2012/35554; (2012); A1;,
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3740-92-9 , The common heterocyclic compound, 3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine, molecular formula is C10H6Cl2N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Under a nitrogen atmosphere, (10 g, 50 mmol) of compound 7-24-5 and (6.1 g, 50 mmol) of compound 9-12-6,(3.5 g, 3 mmol) tetrakis (triphenylphosphine) palladium, (3.2 g, 10 mmol) tetrabutylammonium bromide, (2 g, 50 mmol) sodium hydroxide,(15mL) water and (100mL) toluene were added to a 250mL three-necked flask, and the reaction was heated at 80 C with stirring for 12 hours.Most of the solvent was removed by rotary evaporation of the reaction solution, washed three times with dichloromethane and washed with water. The organic liquid was collected and mixed with silica gel.The yield is 80%

According to the analysis of related databases, 3740-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Huarui Optoelectric Materials Co., Ltd.; He Ruifeng; Lin Weijie; Wu Canjie; Pan Junyou; (40 pag.)CN109970660; (2019); A;,
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289042-12-2, Adding some certain compound to certain chemical reactions, such as: 289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate,molecular formula is C29H40FN3O6S, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 289042-12-2.

Preparation of LDA: To a 500 mL three-necked flask was added 5.75 g of diisopropylamine and 180 mL of THF, three times with nitrogen, nitrogenGas protection, the temperature to -25 (internal temperature), slowly dropping n-BuLi, keep the internal temperature is not higher than -20 , after the dropTo -10 C, continue stirring for 30min, that is, LDA.A solution of ROS01 (10 g) in tetrahydrofuran (50 mL) was cooled to below -70 C, and freshly prepared bisSolution of lithium isopropylamide in tetrahydrofuran was added dropwise. After stirring for 30 min, 1.6 mL of acetone was slowly added dropwise.60min after the addition of 10mL of acetone, reaction 30min, then add 5mL of acetone, the reaction is completed, add 80mL saturated ammonium chlorideThe solution was quenched, separated, and the tetrahydrofuran phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, evaporated to dryness,The crude product was purified by column chromatography (ethyl acetate: petroleum ether = 4: 1) to give the title compound, 4.93 g, 45% yield.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 289042-12-2.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Zhang Zhenfeng; Chen Zhijun; Liu Daobo; Li Dasheng; (8 pag.)CN104557885; (2017); B;,
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213265-83-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Ethyl 5-aminobenzo [b] selenophene-2-carboxylate (1 eq), 4,6-dichloro-5-fluoropyrimidine (3eq)Was dissolved in ethanolUsing a microwave reactor, stir three times for 30 min at 80 C.After completion of the reaction,Solvent was removed from the rotary evaporator and colum.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INDUSTRY ACADEMY COOPERATION FOUNDATION OF SEJONG UNIVERSITY; SAMSUNG LIFE PUBLIC WELFARE FOUNDATION; LIM, DONG-YEOL; CHOI, HONG-LIM; Metrea, Amul; Heo, Su-Yang; Kim, Sun-Young; Nam, Do-Hyun; (55 pag.)KR2017/41562; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 2380-63-4, 1H-Pyrazolo[3,4-d]pyrimidin-4-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 2380-63-4, blongs to pyrimidines compound. 2380-63-4

NIS(1.1eq, 4.95 g, 22 mmol) was slowly added into the mixture of 9(1eq, 2.70 g, 20 mmol) and DMF (50 mL) at r.t. The reaction mixturewas continued stirred at r.t. overnight. The solvent was removed invacuo and water was added. The mixture was subjected to sonicationfor 10 min. The precipitate was collected by filtration, rinsedwith water, and dried. The solid 10 was used for the next stepwithout further purification (5.01 g, 96% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2380-63-4, its application will become more common.

Reference:
Article; He, Linhong; Pei, Heying; Zhang, Chufeng; Shao, Mingfeng; Li, Dan; Tang, Mingli; Wang, Taijing; Chen, Xiaoxin; Xiang, Mingli; Chen, Lijuan; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 96 – 112;,
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3680-71-5, A common compound: 3680-71-5, name is 1,7-Dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one,molecular formula is C6H5N3O, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Phosphorous oxychloride (20 mL) was added to 7H-pyrrolo[2,3-d]pyrimidine-4-ol?(1.15 g, 8.5 mmol) and the reaction was heated under N2?atmosphere to 100 ¡ãC for 2.5 hours. The initial suspension becomes?an?homogeneous dark liquid which was then allowed to cool to room temperature. Excess phosphorous oxychloride was removed?in vacuo?and the residue was cooled in ice bath and crushed ice was added with stirring. The mixture was diluted with water (20 mL) and extracted with ethyl acetate (2 x 30 mL). The combined organic extracts were washed with sat NaCl (aq) solution,?then?dried over anhydrous Na2SO4. Mixture was filtered and filtrate solvents removed in vacuo to afford the title compound as a white solid (0.811 g; (62percent):?LC/MS: RT = 1.619 min;?m/z?= 154 [M+H]+.?Total run time 3.75 mins;?1H NMR (d6?DMSO):?d?6.60 (dd, 1H, J = 3.5, 1.8Hz); 7.69 (dd, 1H, J = 3.6, 2.3 Hz); 8.59 (s,1H), 12.57 (brs 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3680-71-5.

Reference:
Article; Davies, Nicholas G.M.; Browne, Helen; Davis, Ben; Drysdale, Martin J.; Foloppe, Nicolas; Geoffrey, Stephanie; Gibbons, Ben; Hart, Terance; Hubbard, Roderick; Jensen, Michael Rugaard; Mansell, Howard; Massey, Andrew; Matassova, Natalia; Moore, Jonathan D.; Murray, James; Pratt, Robert; Ray, Stuart; Robertson, Alan; Roughley, Stephen D.; Schoepfer, Joseph; Scriven, Kirsten; Simmonite, Heather; Stokes, Stephen; Surgenor, Allan; Webb, Paul; Wood, Mike; Wright, Lisa; Brough, Paul; Bioorganic and Medicinal Chemistry; vol. 20; 22; (2012); p. 6770 – 6789;,
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